San Diego  There’s no denying that San Diego City Attorney Jan Goldsmith is in a unique position in the middle of a strange situation.

As allegations of sexual harassment have snowballed against Mayor Bob Filner, resulting in at least one lawsuit, Goldsmith is caught between defending the city’s liability while also answering to the public who elected him to office.

It’s a high-stakes tightrope that many City Hall and legal observers say Goldsmith seems to be walking well.

But not everybody agrees with his strategy.

Goldsmith forms one side of a sharp legal triangle in the mayor’s sexual harassment case. He is opposed by Filner’s attorney Harvey Berger, one of the top labor lawyers in town, and Gloria Allred, a high-profile women’s rights attorney representing the plaintiff, Irene McCormack Jackson, the mayor’s former director of communications.

So far, it seems we are in for a showdown.

Just two weeks into the lawsuit, Goldsmith has made some aggressive first moves. He’s the first attorney to subpoena for a deposition in the case. He followed up with a cross-complaint, suing Filner in an effort to hold him responsible for any costs the city might incur in the case. Then the City Council voted in closed session not to pay for Filner’s attorney fees.

“If he committed sexual harassment with a city employee, we’re going to be liable for his acts,” Goldsmith told U-T San Diego in an interview last week. “That’s why we sued him in a cross-complaint.”

Former Mayor Jerry Sanders, who worked alongside Goldsmith during the last part of his term, said the city attorney is taking the right approach.

“Jan is going to protect the city. He’s not going to protect any individual. He’s going to protect the taxpayers,” said Sanders. “I think he’s going to do it in a way to make sure the victims aren’t revictimized again.”

Many legal observers expect the case to be settled at some level before trial, a step that often takes place once depositions and discovery have revealed all the facts. As much as 99 percent of civil cases, and notably sexual harassment cases, never make it to trial.

He wrote that cases are evaluated for settlements by experienced lawyers and a risk management team.

“If a case should be settled, we will advise the client at the earliest point possible,” Goldsmith said. “Some cases must got to trial for a variety of reasons.”

Political savvy

Unlike the other two opposing lawyers in the case, Goldsmith is an elected official.

His political resume is long. He was an attorney focusing mostly on real-estate law when he became a Poway city councilman in 1988. At 39, he became Poway’s first elected mayor. He went on to three terms in the state Assembly. He returned to the courtroom as a judge, deciding criminal cases in El Cajon for nine years before stepping into the contentious 2008 city attorney race.

A popular line of his on the campaign trail went like this: “I’ve practiced the law, I’ve written the law, I’ve taught the law and I’ve enforced the law.”

Goldsmith won with 59 percent of the vote to incumbent Michael Aguirre’s 40 percent.

During the campaign, Goldsmith touted himself as the counterpoint to Aguirre in many ways, suggesting he was the respectful adviser to Aguirre’s firebrand contrarian.

While Aguirre gained a reputation as an attack dog, Goldsmith promised to be the city’s watchdog. A Republican, he promised to depoliticize the office and bring back focus to the law.

Some who have watched Goldsmith in office say he has been largely successful in that regard.

“The way he describes it is he’s running one of the biggest law firms in San Diego,” said Republican political consultant John Dadian, adding that Goldsmith’s extensive experience helps him in that role.

But people shouldn’t confuse Goldsmith’s restraint for weakness, Dadian adds.

“Jan is more into getting things done and if that entails being quiet, he’ll take that route,” Dadian said. “And if that entails being forceful, he’ll take that route.”

Goldsmith ran unopposed in the 2012 re-election. He will term out in 2016. He is married to a former prosecutor and Superior Court judge, and the couple has raised three children.

Notable cases

Among Goldsmith’s victories as city attorney are a $27 million settlement negotiated with San Diego Gas & Electric to pay for the city’s losses during the 2007 firestorm. He also won key court rulings on retiree medical benefits, estimated to save the city about $700 million, and pension reform.

When it comes to defending the city and its employees against lawsuits, the office was successful in many cases last year, according to the office’s annual report.

“In many cases, our deputies satisfied either state or federal trial judges that the cases were so lacking in merit that a trial was unnecessary resulting in many frivolous lawsuits being dismissed by the Court without the need for trial,” the report states.

The report does not provide specific data on the amount of cases or on settlements, but includes some examples.

In one of those cases, a city employee sued for racial discrimination and wrongful termination. The city filed motions challenging the legal foundation, and the suit was dismissed.

There have been missteps, too.

The recent prosecution of a man for writing in front of banks with sidewalk chalk gained national attention. The case was issued as a graffiti case, when it should have been a protest case, which falls under different considerations, Goldsmith said. The case prompted changes in issuing guidelines that includes a signoff by supervisors and Goldsmith in protest incidents.

“When we see a problem, we recognize it and correct it,” he said in a written statement.

Some also pointed the finger at Goldsmith for not making sure then-Mayor Sanders signed a key document on funding for the Tourism Marketing District before he left office. When Filner took over, he refused to sign, leaving the funding in limbo.

But others laid the blame with the Sanders administration for not following through.

Legal tactics

The Filner case will surely be one that Goldsmith will be remembered by.

He is not sharing his team’s legal strategy, which outside attorneys say can take a different turn at any point in the case.

Goldsmith’s office is also conducting its own full-scale investigation into the allegations against Filner.

The initial take-charge defense by the city attorney seems spot on, according to many observers.

“I think his approach is very fine-tuned and he seems to be on top of things,” Dadian said.

“The public feels shenanigans are going on with the mayor’s office, and he wants to show the public from his shop that he’s going to do everything completely proper.”

Reactions are mixed how much politics are factoring in to his early decisions in the case.

“I don’t think it’s a result of politics,” said attorney Kenneth Lounsbery, who began his career at the City Attorney’s Office and went on to serve as city attorney of Escondido and San Marcos. “I think it’s a product of hard lawyering.”

Civil attorney Dan Gilleon, on the other hand, described Goldsmith’s tactics as a “political stunt” in which he’s chosen to take the moral high ground and distance himself from anything that might appear to help Filner — perhaps at the risk of brokering a better deal that would lessen the city’s damage.

The city might be better off in the long run working with Filner’s defense, rather than suing him, to negotiate a lower settlement amount that would benefit taxpayers, Gilleon said.

In the end, if Filner can’t pay up, then the city is on the hook anyway, he argued.

But peace between Filner and Goldsmith doesn’t appear in the works anytime soon. Filner, a Democrat, quickly identified Goldsmith as a political rival at the start of his term, rejecting his legal advice and lashing out against him in news conferences. Both have said the feud isn’t personal.

“Generally co-defendants try to make peace. On this case it doesn’t look like peace is an option. This is not good for the defense and certainly advantages the plaintiff,” said former District Attorney Paul Pfingst, who is now in private practice.

Still, Pfingst agreed with many others that Goldsmith seemed to have a good handle on the case.

“I think Jan is behaving in a very even-tempered way. … He has been restrained in this, despite the history of Bob Filner’s not being as restrained in dealing with Jan. Jan is also a creature of politics. But he understands you can still be restrained and still have the same effect,” Pfingst said.

Goldsmith’s former law partner from the 1980s, Brad Hallen, remembered how he would blast off letters and briefs into his Dictaphone “like a machine gun.”

“He’s not flamboyant necessarily in a theatrical way, but absolutely doggedly tenacious as a lawyer,” Hallen said. “When I first started seeing articles on the dispute between the mayor and Jan … I thought, ‘This is not a person you want to make an enemy out of.’”

Goldsmith said his experience as a judge has been “extremely helpful” in dealing with Filner and the case.

Political consultant Dadian went further: “Because of his experience on the judicial bench, his background and training is to take all the facts in and calmly weigh them before making any decisions.”

Leslie Devaney, who served as the second-in-command at the City Attorney’s Office under Casey Gwinn a decade ago, may describe Filner’s unfolding legal case best: “It’s kind of a Rubik’s cube of issues at various levels.”